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Chemical Compound Review

Misodine     5-ethyl-5-phenyl-1,3- diazinane-4,6-dione

Synonyms: Mysoline, Liskantin, Mizodin, Resimatil, primidone, ...
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Disease relevance of primidone


Psychiatry related information on primidone


High impact information on primidone


Chemical compound and disease context of primidone


Biological context of primidone

  • Primidone (PRM) kinetics was examined in two groups of adult seizure patients: (1) 10 newly diagnosed in whom only PRM was used, the monotherapy (MT) group, and (2) nine in whom PRM was added to other antiepileptics, the combination therapy (CT) group [20].
  • The mean value observed for primidone with the on-column alkylation procedure was 9.3 mg/liter and with our procedure was 9.6 mg/liter [21].
  • These results suggest the usefulness of a careful monitoring of primidone and primadone-derived phenobarbitone during pregnancy and the puerperium [22].
  • Fifty specimens were analyzed for primidone and 35 for diphenylhydantoin by a standard gas-chromatographic method involving on-column methylation and by the procedure we have developed [21].
  • Trophozoicidal and cysticidal efficiencies were found to be increased from propamidine to nonamidine; i.e., when the alkyl chain connecting the two benzene rings in their molecular structures was elongated, in comparison with propamidine, hexamidine and octamidine were the most amoebicidal molecules [23].

Anatomical context of primidone


Associations of primidone with other chemical compounds


Gene context of primidone

  • We investigated the association between CYP2C19 polymorphism (possibly related to primidone metabolism) and the risk for developing essential ET and acute adverse effects to primidone [34].
  • The lead compound, hexamidine (1), inhibits not only the proteolytic activity of matriptase, (K(i) = 924 nM) but also of thrombin K(i) = 224 nM) [35].
  • This procedure, compared with the gas-chromatographic procedure of Kupferberg [Clin. Chim. Acta 29, 283 (1970)], gave a weighted regression line--forced through the origin--of y=(1.01+/-0.04) x for phenobarbital, y=(0.95+/-0.04) x for primidone [36].
  • Essential tremor: response to primidone [37].
  • Diphenylhydantoin (PHT) and primidone (PRM) were determined by the EMIT technique in the plasma, tears, saliva, and CSF of epileptic patients [38].

Analytical, diagnostic and therapeutic context of primidone


  1. Delayed fatal agranulocytosis in an epileptic taking primidone and phenytoin. Laurenson, I.F., Buckoke, C., Davidson, C., Gutteridge, C. Lancet (1994) [Pubmed]
  2. Primidone in the treatment of the long QT syndrome: QT shortening and ventricular arrhythmia suppression. DeSilvey, D.L., Moss, A.J. Ann. Intern. Med. (1980) [Pubmed]
  3. Efficacy of primidone in essential tremor. Koller, W.C., Royse, V.L. Neurology (1986) [Pubmed]
  4. A design for the prospective evaluation of the efficacy and toxicity of antiepileptic drugs in adults. Mattson, R.H., Cramer, J.A., Delgado Escueta, A.V., Smith, D.B., Collins, J.F. Neurology (1983) [Pubmed]
  5. Isoniazid as an inhibitor of primidone metabolism. Sutton, G., Kupferberg, H.J. Neurology (1975) [Pubmed]
  6. Comparison of carbamazepine, phenobarbital, phenytoin, and primidone in partial and secondarily generalized tonic-clonic seizures. Mattson, R.H., Cramer, J.A., Collins, J.F., Smith, D.B., Delgado-Escueta, A.V., Browne, T.R., Williamson, P.D., Treiman, D.M., McNamara, J.O., McCutchen, C.B. N. Engl. J. Med. (1985) [Pubmed]
  7. Primidone and rapid cycling affective disorders. Brown, G.M., Stone, G.H., Rathbone, M.P. Lancet (1993) [Pubmed]
  8. The role of technical, biological and pharmacological factors in the laboratory evaluation of anticonvulsant drugs. I. The influence of administration vehicles. Löscher, W., Nolting, B., Fassbender, C.P. Epilepsy Res. (1990) [Pubmed]
  9. A comparison of the effectiveness of primidone versus carbamazepine in epileptic outpatients. Rodin, E.A., Rim, C.S., Kitano, H., Lewis, R., Rennick, P.M. J. Nerv. Ment. Dis. (1976) [Pubmed]
  10. The use of primidone in the treatment of refractory bipolar disorder. Schaffer, L.C., Schaffer, C.B., Caretto, J. Annals of clinical psychiatry : official journal of the American Academy of Clinical Psychiatrists. (1999) [Pubmed]
  11. Single-dose pharmacokinetics and anticonvulsant efficacy of primidone in mice. Leal, K.W., Rapport, R.L., Wilensky, A.J., Friel, P.N. Ann. Neurol. (1979) [Pubmed]
  12. Barbiturate-related connective tissue disorders. Mattson, R.H., Cramer, J.A., McCutchen, C.B. Arch. Intern. Med. (1989) [Pubmed]
  13. Novel anticonvulsant drugs. Stefan, H., Feuerstein, T.J. Pharmacol. Ther. (2007) [Pubmed]
  14. Acute and chronic effects of propranolol and primidone in essential tremor. Koller, W.C., Vetere-Overfield, B. Neurology (1989) [Pubmed]
  15. Two antiepileptic drugs for intractable epilepsy with complex-partial seizures. Schmidt, D. J. Neurol. Neurosurg. Psychiatr. (1982) [Pubmed]
  16. Monomeric serum calcitonin and bone turnover during anticonvulsant treatment and in congenital hypothyroidism. Kruse, K., Süss, A., Büsse, M., Schneider, P. J. Pediatr. (1987) [Pubmed]
  17. Accelerated recovery and disposition from rocuronium in an end-stage renal failure patient on chronic anticonvulsant therapy with sodium valproate and primidone. Driessen, J.J., Robertson, E.N., Booij, L.H., Vree, T.B. British journal of anaesthesia. (1998) [Pubmed]
  18. Serum concentrations of primidone and its metabolites, phenylethylmalonamide and phenobarbital, in the dog. Yeary, R.A. Am. J. Vet. Res. (1980) [Pubmed]
  19. Anticonvulsants in epileptic fowl. Johnson, D.D., Davis, H.L. Arzneimittel-Forschung. (1984) [Pubmed]
  20. Primidone kinetics: effects of concurrent drugs and duration of therapy. Cloyd, J.C., Miller, K.W., Leppik, I.E. Clin. Pharmacol. Ther. (1981) [Pubmed]
  21. Therapeutic monitoring of anticonvulsant drugs: gas-chromatographic simultaneous determination of primidone, phenylethylmalonamide, carbamazepine, and diphenylhydantoin. Least, C.J., Johnson, G.F., Solomon, H.M. Clin. Chem. (1975) [Pubmed]
  22. Changes in primidone/phenobarbitone ratio during pregnancy and the puerperium. Battino, D., Binelli, S., Bossi, L., Como, M.L., Croci, D., Cusi, C., Avanzini, G. Clinical pharmacokinetics. (1984) [Pubmed]
  23. Amoebicidal efficiencies of various diamidines against two strains of Acanthamoeba polyphaga. Perrine, D., Chenu, J.P., Georges, P., Lancelot, J.C., Saturnino, C., Robba, M. Antimicrob. Agents Chemother. (1995) [Pubmed]
  24. Primidone but not phenylethylmalonamide, a major metabolite, increases nerve-evoked transmitter release at the frog neuromuscular junction. Talbot, P.A., Alderdice, M.T. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  25. Anticonvulsant level in saliva, serum, and cerebrospinal fluid. Troupin, A.S., Friel, P. Epilepsia (1975) [Pubmed]
  26. Overflow urinary incontinence due to carbamazepine. Anders, R.J., Wang, E., Radhakrishnan, J., Sharifi, R., Lee, M. J. Urol. (1985) [Pubmed]
  27. Microassay for primidone and its metabolites phenylethylmalondiamide, phenobarbital and p-hydroxyphenobarbital in human serum, saliva, breast milk and tissues by gas chromatography--mass spectrometry using selected ion monitoring. Nau, H., Jesdinsky, D., Wittfoht, W. J. Chromatogr. (1980) [Pubmed]
  28. Rapid micro-method for the measurement of phenobarbitone, primidone and phenytoin in blood plasma or serum by gas-liquid chromatography. Rutherford, D.M., Flanagan, R.J. J. Chromatogr. (1978) [Pubmed]
  29. Causes of treatment failure with antiepileptic drugs vary over time. Homan, R.W., Miller, B. Neurology (1987) [Pubmed]
  30. Adjuvant therapy of parkinsonian tremor. Koller, W.C., Herbster, G. Arch. Neurol. (1987) [Pubmed]
  31. Pharmacokinetics of phenylethylmalonamide (PEMA) after oral and intravenous administration. Pisani, F., Richens, A. Clinical pharmacokinetics. (1983) [Pubmed]
  32. Acetazolamide-induced interference with primidone absorption. Case reports and metabolic studies. Syversen, G.B., Morgan, J.P., Weintraub, M., Myers, G.J. Arch. Neurol. (1977) [Pubmed]
  33. Pharmacology of cortical epileptic afterdischarges in rats. Kubova, H., Lanstiakova, M., Mockova, M., Mares, P., Vorlicek, J. Epilepsia (1996) [Pubmed]
  34. CYP2C19 Polymorphism and Risk for Essential Tremor. Alonso-Navarro, H., Mart??nez, C., Garc??a-Mart??n, E., Benito-Le??n, J., Garc??a-Ferrer, I., V??zquez-Torres, P., Puertas, I., L??pez-Alburquerque, T., Ag??ndez, J.A., Jim??nez-Jim??nez, F.J. Eur. Neurol. (2006) [Pubmed]
  35. Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase. Enyedy, I.J., Lee, S.L., Kuo, A.H., Dickson, R.B., Lin, C.Y., Wang, S. J. Med. Chem. (2001) [Pubmed]
  36. Anticonvulsants in serum, determined with a fully mechanized enzyme analyzer. McClean, S.W., Young, D.S., Yonekawa, W. Clin. Chem. (1977) [Pubmed]
  37. Essential tremor: response to primidone. Chakrabarti, A., Pearce, J.M. J. Neurol. Neurosurg. Psychiatr. (1981) [Pubmed]
  38. Diphenylhydantoin and primidone in tears. Monaco, F., Piredda, S., Mastropaolo, C., Tondi, M., Mutani, R. Epilepsia (1981) [Pubmed]
  39. Rapid measurement of free anticonvulsant drugs by direct liquid chromatography of serum ultrafiltrates. Bock, J.L., Ben-Ezra, J. Clin. Chem. (1985) [Pubmed]
  40. Determination of primidone by electron-capture gas chromatography. Wallace, J.E., Hamilton, H.E., Shimek, E.L., Schwertner, H.A., Blum, K. Anal. Chem. (1977) [Pubmed]
  41. Primidone analyses: correlation of gas-chromatographic assay with enzyme immunoassay. Sun, L., Walwick, E.R. Clin. Chem. (1976) [Pubmed]
  42. Fluorescent immunoassay for determining antiepileptic drug concentrations: clinical usefulness. Smith, D.B., Carl, G.F. Arch. Neurol. (1982) [Pubmed]
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